Benzyl Bromide → 5-Acetyl-1,3-dibenzyluracil

HRID 1297143Notes

Reaction equation

HRID 1297143 reaction equation
[C:1]([C:4]1[C:5](=O)[NH:6][C:7](=[O:10])[NH:8][CH:9]=1)(=[O:3])[CH3:2].[C:12](=[O:15])([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[C:1]([C:4]1[C:12](=[O:15])[N:8]([CH2:9][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:7](=[O:10])[N:6]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2345815-Acetyluracil

Product 1

HCID 116744085-Acetyl-1,3-dibenzyluracilYield 79.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 5-acetyluracil (3.1 g, 20 mmol), and potassium carbonate (6.9 g, 50 mmol) in DMF (75 ml) was stirred for 20 min. Then benzyl bromide (6.0 ml, 50 mmol) was added. The resulting mixture was stirred for 8 h at room temperature. DMF was distilled under vacuum. The residue was purified by column (dichloromethane:methanol 40:1). The appropriate fraction was concentrated and crystallized from ethanol to afford 5.34 g of a white solid. Yield was 79.8%. Mp. 92-93° C. 1HNMR (CDCl3): 8.23 (s, 1H), 7.29-7.49 (m, 10H), 5.17 (s, 2H), 5.01 (s, 2H), 2.62 (s, 3H). 13CNMR (CDCl3): 194.5, 160.7, 151.0, 148.4, 136.2, 134.4, 129.2, 129.0, 128.9, 128.5, 128.2, 127.8, 112.2, 53.4, 44.9, 30.7. FAB-HRMS: [M+H]+ calcd. for C20H19N2O3 335.1396, found 335.1412.

Workup

  1. stirringThe resulting mixture was stirred for 8 h at room temperature
  2. distillationDMF was distilled under vacuum
  3. customThe residue was purified by column (dichloromethane:methanol 40:1)
  4. concentrationThe appropriate fraction was concentrated
  5. customcrystallized from ethanol

Sources & evidence

ORD record
ord-8574972df5a543168d5832c78c16e4fc
Source dataset
uspto-grants-2007_07
Patent number
US07250421B2

Reaction notes

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